RU2509773C2 - Дейтерированные бензилбензольные производные и способы применения - Google Patents
Дейтерированные бензилбензольные производные и способы применения Download PDFInfo
- Publication number
- RU2509773C2 RU2509773C2 RU2011105422/04A RU2011105422A RU2509773C2 RU 2509773 C2 RU2509773 C2 RU 2509773C2 RU 2011105422/04 A RU2011105422/04 A RU 2011105422/04A RU 2011105422 A RU2011105422 A RU 2011105422A RU 2509773 C2 RU2509773 C2 RU 2509773C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- cycloalkyl
- alkenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 15
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 33
- 229910052805 deuterium Inorganic materials 0.000 claims abstract 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract 16
- -1 diaryl methyl compound Chemical class 0.000 claims abstract 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 201000010099 disease Diseases 0.000 claims abstract 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract 4
- 230000005764 inhibitory process Effects 0.000 claims abstract 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract 3
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims abstract 2
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract 2
- 206010012655 Diabetic complications Diseases 0.000 claims abstract 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims abstract 2
- 206010020772 Hypertension Diseases 0.000 claims abstract 2
- 201000001431 Hyperuricemia Diseases 0.000 claims abstract 2
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract 2
- 208000008589 Obesity Diseases 0.000 claims abstract 2
- 206010030113 Oedema Diseases 0.000 claims abstract 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract 2
- 201000001421 hyperglycemia Diseases 0.000 claims abstract 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims abstract 2
- 201000008980 hyperinsulinism Diseases 0.000 claims abstract 2
- 235000020824 obesity Nutrition 0.000 claims abstract 2
- 208000011580 syndromic disease Diseases 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 4
- 102000018711 Facilitative Glucose Transport Proteins Human genes 0.000 claims 4
- 108091052347 Glucose transporter family Proteins 0.000 claims 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- 229910052708 sodium Inorganic materials 0.000 claims 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 3
- 239000006185 dispersion Substances 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical group OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims 2
- 230000000155 isotopic effect Effects 0.000 claims 2
- 239000002480 mineral oil Substances 0.000 claims 2
- 235000010446 mineral oil Nutrition 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims 2
- 239000012312 sodium hydride Substances 0.000 claims 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- 229930182821 L-proline Natural products 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims 1
- 230000016507 interphase Effects 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- 229960002429 proline Drugs 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 150000005621 tetraalkylammonium salts Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 abstract 2
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 abstract 2
- 102100037202 Sodium/myo-inositol cotransporter 2 Human genes 0.000 abstract 1
- 101710090560 Sodium/myo-inositol cotransporter 2 Proteins 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 CC=Cc1ccc(C(*)(*)c2cc([C@@]([C@]([C@@]3O)O)OC(CO)[C@]3O)ccc2Cl)cc1 Chemical compound CC=Cc1ccc(C(*)(*)c2cc([C@@]([C@]([C@@]3O)O)OC(CO)[C@]3O)ccc2Cl)cc1 0.000 description 5
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13496808P | 2008-07-15 | 2008-07-15 | |
| US61/134,968 | 2008-07-15 | ||
| PCT/US2009/050710 WO2010009243A1 (en) | 2008-07-15 | 2009-07-15 | Deuterated benzylbenzene derivatives and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011105422A RU2011105422A (ru) | 2012-08-20 |
| RU2509773C2 true RU2509773C2 (ru) | 2014-03-20 |
Family
ID=41550702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011105422/04A RU2509773C2 (ru) | 2008-07-15 | 2009-07-15 | Дейтерированные бензилбензольные производные и способы применения |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9061060B2 (https=) |
| EP (1) | EP2312944B1 (https=) |
| JP (2) | JP6071198B2 (https=) |
| CN (1) | CN102149280B (https=) |
| AR (1) | AR072511A1 (https=) |
| AU (1) | AU2009270936B2 (https=) |
| BR (1) | BRPI0916769A2 (https=) |
| CA (1) | CA2730734C (https=) |
| IL (1) | IL210582A (https=) |
| MX (1) | MX2011000637A (https=) |
| RU (1) | RU2509773C2 (https=) |
| TW (1) | TWI523652B (https=) |
| UA (1) | UA104594C2 (https=) |
| WO (1) | WO2010009243A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2541141T3 (es) * | 2008-01-31 | 2015-07-16 | Astellas Pharma Inc. | Composición farmacéutica para el tratamiento de las enfermedades del hígado graso |
| AU2009270936B2 (en) * | 2008-07-15 | 2014-12-18 | Theracos, Inc. | Deuterated benzylbenzene derivatives and methods of use |
| MX2011001855A (es) * | 2008-08-22 | 2011-03-24 | Theracos Inc | Procesos para la preparacion de inhibidores de sglt2. |
| US20100167988A1 (en) * | 2008-10-22 | 2010-07-01 | Auspex Pharmaceuticals, Inc. | Ethoxyphenylmethyl inhibitors of sglt2 |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| CN102134226B (zh) * | 2010-01-26 | 2013-06-12 | 天津药物研究院 | 一类苯基c-葡萄糖苷衍生物、其制备方法和用途 |
| TWI599360B (zh) | 2010-05-11 | 2017-09-21 | 健生藥品公司 | 醫藥調配物 |
| WO2011153712A1 (en) | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| CN102372722A (zh) * | 2010-08-10 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用 |
| RS55056B1 (sr) | 2011-04-13 | 2016-12-30 | Janssen Pharmaceutica Nv | Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2 |
| KR101609859B1 (ko) * | 2011-04-25 | 2016-04-07 | 베이징 프릴루드 팜. 에스씨아이. & 테크. 씨오., 엘티디. | 소듐-의존적 포도당 운반 단백질의 억제제 및 이의 제조방법 및 용도 |
| TWI542596B (zh) * | 2011-05-09 | 2016-07-21 | 健生藥品公司 | (2s,3r,4r,5s,6r)-2-(3-((5-(4-氟苯基)噻吩-2-基)甲基)-4-甲基苯基)-6-(羥甲基)四氫-2h-哌喃-3,4,5-三醇之l-脯胺酸及檸檬酸共晶體 |
| CN103889429B (zh) * | 2011-10-31 | 2016-10-19 | 台湾神隆股份有限公司 | Sglt2抑制剂的结晶和非结晶形式 |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| CN102942840B (zh) * | 2012-11-05 | 2017-04-12 | 大连理工大学 | 一种具有强粘附性的导电高分子聚苯胺/三氧化二锰复合涂层及其制法 |
| CN103910719B (zh) * | 2012-12-31 | 2018-05-01 | 上海璎黎药业有限公司 | 葡萄糖衍生物与苯丙氨酸复合物、晶体、制备方法及应用 |
| JP5646706B2 (ja) * | 2013-07-24 | 2014-12-24 | 壽製薬株式会社 | C−グリコシド誘導体の製造方法 |
| WO2015051484A1 (en) * | 2013-10-12 | 2015-04-16 | Theracos, Inc. | Preparation of hydroxy-benzylbenzene derivatives |
| WO2015063726A1 (en) * | 2013-10-31 | 2015-05-07 | Ranbaxy Laboratories Limited | Process for the preparation of 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene |
| MX376097B (es) * | 2013-12-17 | 2025-03-07 | Boehringer Ingelheim Vetmedica Gmbh | Inhibidores de sglt2 para usarse en el tratamiento o prevención de trastornos metabólicos en animales felinos. |
| CN104478670B (zh) * | 2014-11-17 | 2016-08-17 | 中国药科大学 | 5-溴-2-氯-4’-乙氧基二苯甲烷的制备方法 |
| CN105753910A (zh) * | 2014-12-16 | 2016-07-13 | 康普药业股份有限公司 | 一种卡格列净中间体的制备方法 |
| CN107698620A (zh) * | 2015-06-23 | 2018-02-16 | 江苏天士力帝益药业有限公司 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
| CN110551088B (zh) * | 2018-06-01 | 2022-10-21 | 北京惠之衡生物科技有限公司 | 氘修饰的苄基-4-氯苯基的c-糖苷衍生物 |
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- 2009-07-15 AR ARP090102683A patent/AR072511A1/es unknown
- 2009-07-15 CN CN200980135856.7A patent/CN102149280B/zh not_active Expired - Fee Related
- 2009-07-15 JP JP2011518883A patent/JP6071198B2/ja not_active Expired - Fee Related
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- 2009-07-15 EP EP09798706.9A patent/EP2312944B1/en not_active Not-in-force
- 2009-07-15 TW TW098123938A patent/TWI523652B/zh not_active IP Right Cessation
- 2009-07-15 MX MX2011000637A patent/MX2011000637A/es unknown
- 2009-07-15 UA UAA201101753A patent/UA104594C2/uk unknown
- 2009-07-15 RU RU2011105422/04A patent/RU2509773C2/ru not_active IP Right Cessation
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- 2011-01-12 IL IL210582A patent/IL210582A/en not_active IP Right Cessation
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Also Published As
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|---|---|
| IL210582A (en) | 2015-08-31 |
| IL210582A0 (en) | 2011-03-31 |
| CA2730734A1 (en) | 2010-01-21 |
| EP2312944A4 (en) | 2012-08-29 |
| EP2312944A1 (en) | 2011-04-27 |
| JP2011528370A (ja) | 2011-11-17 |
| UA104594C2 (en) | 2014-02-25 |
| AR072511A1 (es) | 2010-09-01 |
| MX2011000637A (es) | 2011-05-02 |
| RU2011105422A (ru) | 2012-08-20 |
| EP2312944B1 (en) | 2018-09-05 |
| US9061060B2 (en) | 2015-06-23 |
| US20100063141A1 (en) | 2010-03-11 |
| BRPI0916769A2 (pt) | 2017-09-26 |
| JP2015134773A (ja) | 2015-07-27 |
| AU2009270936B2 (en) | 2014-12-18 |
| JP6071198B2 (ja) | 2017-02-01 |
| CN102149280B (zh) | 2017-05-24 |
| WO2010009243A1 (en) | 2010-01-21 |
| CA2730734C (en) | 2017-04-25 |
| CN102149280A (zh) | 2011-08-10 |
| TW201010696A (en) | 2010-03-16 |
| AU2009270936A1 (en) | 2010-01-21 |
| TWI523652B (zh) | 2016-03-01 |
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